Abstract
R. J. ANDERSON1 gave the name ‘mycolic acid’ to a high-molecular weight fatty acid (m.p. 58°), isolated from the H 37 strain of Mycobacterium tuberculosis var. hominis. The structural features of mycolic acid, as elucidated by him, are as follows: its probable formula is C88H176O4, with one—COOH, one—OH and one—OCH3 group ; pyrolysis at 300° in a vacuum gives a volatile distillate (m.p. 88°), identified as n-hexacosanoic acid, C26H52O2. Chromic acid oxidation breaks up mycolic acid into smaller fragments, among which the following could be identified: stearic acid, n-hexacosanoic acid and hexadecane, 1, 16-dicarboxylic acid2.
This is a preview of subscription content, access via your institution
Access options
Subscribe to this journal
Receive 51 print issues and online access
$199.00 per year
only $3.90 per issue
Buy this article
- Purchase on Springer Link
- Instant access to full article PDF
Prices may be subject to local taxes which are calculated during checkout
Similar content being viewed by others
References
Stodola, F. H., Lesuk, A., and Anderson, R. J., J. Biol. Chem., 126, 505 (1938).
Lesuk, A., and Anderson, R. J., J. Biol. Chem., 136, 603 (1940).
Cason, J., and Anderson, R. J., J. Biol. Chem., 126, 527 (1938).
Anderson, R. J., and Creighton, M. M., J. Biol. Chem., 129, 57 (1939).
Peck, R. L., and Anderson, R. J., J. Biol. Chem., 140, 89 (1941).
Anderson, R. J., Crowder, J. A., Newman, M. S., and Stodola, F. H., J. Biol. Chem., 113, 637 (1936).
Ställberg-Stenhagen, S., and Stenhagen, E., J. Biol. Chem., 165, 599 (1946).
Asselineau, J., and Lederer, E., Bull. Soc. Chim. Biol., 31, 492 (1949).
Asselineau, J., and Lederer, E., C.R. Acad. Sci., Paris, 228, 1892 (1949).
Asselineau, J., C.R. Acad. Sci., Paris, 230, 1620 (1950).
Schnapp, H., Liebigs Ann., [201, 62 (1880). Jones, E. J., Liebigs Ann., 226, 287 (1884).
One alkyl group in a is sufficient for pyrolysis, as O. Wallach, (Liebigs Ann., 365, 255; 1909) has shown that a-(1-hydroxy, 3-methyl,5-isopropyl-cyclohexyl)propionic acid pyrolyses to menthone + n-propionic acid.
From a monolayer and X-ray study of mycolic acid, S. Ställberg-Stenhagen and E. Stenhagen (J. Biol. Chem., 159, 255; 1945) concluded that: “the cross-section of the molecule at no part of its length can be larger than that occupied by three parallel hydrocarbon chains”.
Asselineau, J., Demarteau, H., and Lederer, E., C.R. Acad. Sci., Paris, 230, 877 (1950), and unpublished work of the authors with Demarteau, H., and Ginsburg, A.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
ASSELINEAU, J., LEDERER, E. Structure of the Mycolic Acids of Mycobacteria. Nature 166, 782–783 (1950). https://doi.org/10.1038/166782a0
Issue Date:
DOI: https://doi.org/10.1038/166782a0
This article is cited by
-
In Silico Drug Design of Thiolactomycin Derivatives Against Mtb-KasA Enzyme to Inhibit Multidrug Resistance of Mycobacterium tuberculosis
Interdisciplinary Sciences: Computational Life Sciences (2019)
-
The influence of AccD5 on AccD6 carboxyltransferase essentiality in pathogenic and non-pathogenic Mycobacterium
Scientific Reports (2017)
-
Adaptive response of Rhodococcus opacus PWD4 to salt and phenolic stress on the level of mycolic acids
AMB Express (2016)
-
Mechanisms of β-lactam killing and resistance in the context of Mycobacterium tuberculosis
The Journal of Antibiotics (2014)
-
Pharmacophore combination as a useful strategy to discover new antitubercular agents
Medicinal Chemistry Research (2014)
Comments
By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.
